<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <id type="integer">4020</id>
  <title>T3D3966</title>
  <common-name>Enterodiol</common-name>
  <description>Enterodiol is one of the most important lignan-type phytoestrogens identified in serum, urine, bile and seminal fluids of humans and animals. Phytoestrogens are a diverse group of compounds found in many edible plants that have, as their common denominator, a phenolic group that they share with estrogenic steroids. This phenolic group appears to play an important role in determining the estrogenic agonist/antagonistic properties of these compounds. Phytoestrogens have been categorized according to their chemical structures as isoflavones, lignans and coumestans. Enterodiol is formed by bacteria in the intestinal tract from the plant lignans matairesinol and secoisolariciresinol, which exist in various whole-grain cereals (barley, rye and wheat), seeds, nuts, legumes and vegetables.  (A3194).</description>
  <cas>80226-00-2</cas>
  <pubchem-id>115089</pubchem-id>
  <chemical-formula>C18H22O4</chemical-formula>
  <weight nil="true"/>
  <appearance>White powder.</appearance>
  <melting-point></melting-point>
  <boiling-point></boiling-point>
  <density nil="true"/>
  <solubility></solubility>
  <specific-gravity nil="true"/>
  <flash-point nil="true"/>
  <vapour-pressure nil="true"/>
  <route-of-exposure nil="true"/>
  <target nil="true"/>
  <mechanism-of-toxicity nil="true"/>
  <metabolism nil="true"/>
  <toxicity nil="true"/>
  <lethaldose nil="true"/>
  <carcinogenicity>No indication of carcinogenicity to humans (not listed by IARC).</carcinogenicity>
  <use-source>Phytoestrogens are a diverse group of compounds found in many edible plants that have, as their common denominator, a phenolic group that they share with estrogenic steroids.</use-source>
  <min-risk-level nil="true"/>
  <health-effects nil="true"/>
  <symptoms nil="true"/>
  <treatment nil="true"/>
  <created-at type="dateTime">2014-08-29T04:47:56Z</created-at>
  <updated-at type="dateTime">2026-04-05T16:32:45Z</updated-at>
  <interacting-proteins nil="true"/>
  <wikipedia nil="true"/>
  <uniprot-id nil="true"/>
  <kegg-compound-id>C18166</kegg-compound-id>
  <omim-id nil="true"/>
  <chebi-id>544560</chebi-id>
  <biocyc-id nil="true"/>
  <ctd-id nil="true"/>
  <stitch-id nil="true"/>
  <drugbank-id nil="true"/>
  <pdb-id nil="true"/>
  <actor-id nil="true"/>
  <organism nil="true"/>
  <export type="boolean">true</export>
  <metabolizing-proteins nil="true"/>
  <transporting-proteins nil="true"/>
  <moldb-smiles>OC[C@H](CC1=CC(O)=CC=C1)[C@H](CO)CC1=CC(O)=CC=C1</moldb-smiles>
  <moldb-formula>C18H22O4</moldb-formula>
  <moldb-inchi>InChI=1S/C18H22O4/c19-11-15(7-13-3-1-5-17(21)9-13)16(12-20)8-14-4-2-6-18(22)10-14/h1-6,9-10,15-16,19-22H,7-8,11-12H2/t15-,16-/m0/s1</moldb-inchi>
  <moldb-inchikey>DWONJCNDULPHLV-HOTGVXAUSA-N</moldb-inchikey>
  <moldb-average-mass type="decimal">302.3649</moldb-average-mass>
  <moldb-mono-mass type="decimal">302.151809192</moldb-mono-mass>
  <origin>Exogenous</origin>
  <state>Solid</state>
  <logp nil="true"/>
  <hmdb-id>HMDB05056</hmdb-id>
  <chembl-id>CHEMBL471076</chembl-id>
  <chemspider-id>102992</chemspider-id>
  <structure-image-file-name nil="true"/>
  <structure-image-content-type nil="true"/>
  <structure-image-file-size type="integer" nil="true"/>
  <structure-image-updated-at type="dateTime" nil="true"/>
  <biodb-id nil="true"/>
  <synthesis-reference>Mahalanabis, K. K.; Mumtax, M.; Snieckuz, V.  Dimetalated tertiary succinamides.  Synthesis of several classes of lignans including the mammalian urinary lignans enterolactone and enterodiol.    Tetrahedron Letters  (1982),  23(39),  3975-8. </synthesis-reference>
  <structure-image-caption nil="true"/>
  <chemdb-id>CHEM002926</chemdb-id>
  <dsstox-id>DTXSID0047876</dsstox-id>
  <toxcast-id nil="true"/>
  <stoff-ident-origin nil="true"/>
  <stoff-ident-id nil="true"/>
  <susdat-id>NS00076968</susdat-id>
  <iupac nil="true"/>
  <moldb-polar-surface-area>80.92</moldb-polar-surface-area>
  <moldb-refractivity>86.36060000000002</moldb-refractivity>
  <moldb-polarizability>32.76260824205408</moldb-polarizability>
  <moldb-rotatable-bond-count>7</moldb-rotatable-bond-count>
  <moldb-acceptor-count>4</moldb-acceptor-count>
  <moldb-donor-count>4</moldb-donor-count>
  <moldb-pka-strongest-acidic>9.793418141582793</moldb-pka-strongest-acidic>
  <moldb-pka-strongest-basic>-2.603209181436301</moldb-pka-strongest-basic>
  <moldb-physiological-charge>0</moldb-physiological-charge>
  <moldb-number-of-rings>2</moldb-number-of-rings>
  <moldb-alogps-logp>1.91</moldb-alogps-logp>
  <moldb-alogps-logs>-4.09</moldb-alogps-logs>
  <moldb-alogps-solubility>2.47e-02 g/l</moldb-alogps-solubility>
</compound>
